The existing historical literature on the financing of a modern steel industry in the United States is characterised by a major disagreement. One view, advanced by Lance Davis, is that the steel industry’s expansion was constrained by a lack of external finance given limited markets for iron and steel securities in the United States in the post-bellum decades. A contrasting perspective, developed by Alfred Chandler, is that external finance mattered little to pioneering steel enterprises given their privileged access to internal resources. Both historians take the Carnegie steel business as their crucial reference point, although Davis considers it an exception while Chandler treats it as rule. This paper seeks to broaden our purview by analysing the financing of three Chicago-based steel companies which ranked among the most formidable of Carnegie’s rivals during the early development of America’s modern steel industry. It shows that a different starting point leads to a fresh perspective on the important issues that Davis and Chandler raise. Contrary to Chandler’s claims, none of these three Chicago steel makers had sufficient internal resources at its disposal to be financially autonomous. All of them were heavily dependent on external finance to fund their expansion, and to survive the periodic crises that plagued the fledgling U.S. steel industry, and notwithstanding Davis’ arguments, they all succeeded in raising large amounts of external finance. Outside money came from local capitalists as well as more distant ones, including some of the most prominent financiers in the country, but in all cases we observe a personal capitalism with financiers investing their own money, and that of their family and friends, in enterprises with which they had direct contact. These relationships allowed for the financial flexibility necessary to respond to the uncertainties that were integral to pioneering steel enterprises’ activities. However, to function effectively, these relationships depended on trust by financiers in the men operating the iron and steel business. When trust broke down, contracts assumed a greater role but, as we shall see, they proved far from satisfactory and their shortcomings provide important insight into the obstacles to the development of markets for iron and steel securities in the United States at this time.